Rapid Transformation of D-Mannose into Orthogonally Protected D-Glucosamine and D-Galactosamine Thioglycosides

被引：40

作者：

Emmadi, Madhu ^{[1
]}

Kulkarni, Suvarn S. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 11期

关键词：

ONE-POT PROTECTION; EFFICIENT SYNTHESIS; DERIVATIVES; OLIGOSACCHARIDES; ROUTE; AZIDE; 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE; SUBSTITUTION; CONVERSION; MECHANISM;

D O I：

10.1021/jo200342v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expedient protocol for synthesis of orthogonally protected 2-azido-2-deoxy-D-glucosamine and 2-azido-2-deoxy-D-galactosamine donors from D-mannose is described. Readily available phenyl,beta-D-thiomannoside is rapidly transformed into D-GlcN(3) thioglycosides via a highly regioselective 3-O-acylation followed by 4,6-O-benzylidenation and azide displacement of C-2-OTf, which is further converted into D-GalN(3) thioglycosides through Lattrell-Dax inversion of the C4 hydroxy group and its Boc protection. The reaction sequence may be completed in 2 days and involves simple workups and minimal column chromatography.

引用

页码：4703 / 4709

页数：7

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